Hydrochloric Acid → HCID 20441658, compound

HRID 1633149Notes

Reaction equation

HRID 1633149 reaction equation
C([CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)#N.C[Mg]Br.Cl.CC[O:29][CH2:30][CH3:31]>>[O:29]=[C:30]([CH3:31])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[C:8]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 13362115HCID 13362115, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 20441658HCID 20441658, compound

Procedure

1-(4-cyanobutyl)-3-methyl-2-(3-pyridyl)indole (1.5 g) in 15 ml of ether is added to a solution of 0.0103 mole of methyl magnesium bromide in 15 ml of ether, and this mixture is heated at reflux temperature for 3 hours. After cooling, 10 ml of 6N HCl is added dropwise and this mixture refluxed for several hours. The reaction mixture is washed with ether, and basified to pH 10-11 with 3N NaOH. Ether extraction and evaporation of the solvent yields 1-(5-oxohexyl)-3-methyl-2-(3-pyridyl)- indole; IR 1720 cm-1 ; NMR (CDCl3)δ2.0.

Workup

  1. temperaturethis mixture is heated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureAfter cooling
  4. temperaturethis mixture refluxed for several hours
  5. washThe reaction mixture is washed with ether
  6. extractionEther extraction and evaporation of the solvent

Sources & evidence

ORD record
ord-1502c351de7c47bcaa02761804a846eb
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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